Hi Barrman and welcome to the forum.
The question of chartering to pay for a boat or to fund the lifestyle is pretty common but your idea is a bit different. It could work to at least supplement your live aboard life but there's a number of things you should consider.
- Day sails
and harbor tours are very common in all tourist destinations I've been to. A lot of them are so called booze cruises where a boat, frequently a cat, takes a crowd (often a big crowd) out around the harbor with music
or snacks, and of course booze. These are usually very popular and during peak tourist seasons are frequently packed.
More personal tours, snorkeling trips or sunset sails
with couples or small groups are also common but less popular. These usually cost the customer a lot more than the booze cruise
and in general not as regular, reliable business for the operator.
So the booze cruises can generate a good bit of business but you need the room to hold them and also have to deal with mobs of rowdy tourists barging around in your home.
- Anywhere you do this you will have red tape
to deal with. Possibly a lot. If non-US territory you have to deal with work permits, just like a foreigner trying to work in the US. If there are locals doing the same business getting a permit
to compete against them could be difficult. Try to do it under the radar
you will almost certainly get busted by the locals complaining to their cousin who's the local constable.
If US territory if I recall
correctly you have to have a boat that is USCG inspected if you carry more than 6 passengers. This entails complying with a whole lot of safety regulations
. You will certainly need a USCG captains license
Please note that the above comments are very general and just intended as a very rough guide to the issue. Local situations can be quite different.